6 Alpha, 6 beta-difluoro-etianic acid derivatives

Abstract

Certain 3-ketoandrost-4-ene and 3-ketoandrosta-1,4-diene 17 beta-carboxylic acids and esters substituted at the 6 alpha and 6 beta positions with fluorine substituents are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9 alpha position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9 alpha-chloro); substituted at 16 alpha (or 16 beta) with methyl or hydrogen when there is a 17 alpha-hydroxy (or an ester).

What is claimed is: 
     
       1. A compound chosen from those represented by the formula ##STR12## wherein X 1  is chloro; X 2  is ##STR13##  R is hydrogen, alkyl or 1 through 6 carbon atoms optionally substituted with one of halo, phenyl or benzyl ring chosen from the group consisting of alkyl of 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms and halo;   R 1  is hydrogen or alkanoyl of 2 through 6 carbon atoms;   R 2  is hydrogen, alpha-methyl or beta-methyl; and   the broken line between C-1 and C-2 represents a double or a single bond.   
     
     
       2. The compound of claim 1 wherein R 2  is alpha-methyl. 
     
     
       3. The compound of claim 2 wherein R is hydrogen, alkyl of 1 to 6 carbon atoms, phenyl or benzyl and R 1  is hydrogen or alkanoyl of 1 through 6 carbon atoms. 
     
     
       4. The compound of claim 3 wherein X 1  is chloro and X 2  is ##STR14## 
     
     
       5. The compound of claim 4 wherein the bond between C-1 and C-2 is a double bond, R is methyl and R 1  is propionyl, namely methyl 9 alpha, 11 beta-dichloro-6 alpha, 6 beta-difluoro-16 alpha-methyl-3-oxo-propionyloxyandrosta-1,4-diene 17 betacarboxylate. 
     
     
       6. An anti-inflammatory pharmaceutical composition which comprises an effective amount of a compound of claim 1 in combination with a suitable pharmaceutical excipient. 
     
     
       7. A process for treating an inflamed condition in a mammal which comprises adminstering an effective amount of a compound of claim 1 to said mammal. 
     
     
       8. A process for treating an inflamed condition in a mammal which comprises administering an effective amount of a compound of claim 1 to said mammal.